PT1529032E - Processos para a preparação de 4-[[(4-[[4-(2-cianoetenilo)-2,6 dimetilofenilo]amino]-2-pirimidinilo]amino]benzonitrilo - Google Patents
Processos para a preparação de 4-[[(4-[[4-(2-cianoetenilo)-2,6 dimetilofenilo]amino]-2-pirimidinilo]amino]benzonitrilo Download PDFInfo
- Publication number
- PT1529032E PT1529032E PT37878139T PT03787813T PT1529032E PT 1529032 E PT1529032 E PT 1529032E PT 37878139 T PT37878139 T PT 37878139T PT 03787813 T PT03787813 T PT 03787813T PT 1529032 E PT1529032 E PT 1529032E
- Authority
- PT
- Portugal
- Prior art keywords
- addition salt
- acid addition
- formula
- amino
- stereochemically isomeric
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims description 51
- 230000008569 process Effects 0.000 title claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 title description 6
- HLCPWBZNUKCSBN-UHFFFAOYSA-N 2-aminobenzonitrile Chemical compound NC1=CC=CC=C1C#N HLCPWBZNUKCSBN-UHFFFAOYSA-N 0.000 title 1
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- 150000003839 salts Chemical class 0.000 claims description 96
- 239000002253 acid Substances 0.000 claims description 91
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- 150000001412 amines Chemical group 0.000 claims description 49
- -1 4 - [[4 - [[4- (2-cyanoethenyl) -2,6-dimethylphenyl] amino] -2-pyridinyl] amino] benzonitrile Chemical compound 0.000 claims description 40
- 239000003054 catalyst Substances 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 34
- 238000006243 chemical reaction Methods 0.000 claims description 33
- 229910052763 palladium Inorganic materials 0.000 claims description 33
- 238000011282 treatment Methods 0.000 claims description 28
- 150000001204 N-oxides Chemical class 0.000 claims description 22
- 239000012458 free base Substances 0.000 claims description 20
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical group CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 18
- 125000000815 N-oxide group Chemical group 0.000 claims description 17
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
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- WMKGGPCROCCUDY-PHEQNACWSA-N dibenzylideneacetone Chemical compound C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 WMKGGPCROCCUDY-PHEQNACWSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
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- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
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- 150000004965 peroxy acids Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- MISVBCMQSJUHMH-UHFFFAOYSA-N pyrimidine-4,6-diamine Chemical class NC1=CC(N)=NC=N1 MISVBCMQSJUHMH-UHFFFAOYSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
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- 235000019698 starch Nutrition 0.000 description 1
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- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/14—Antivirals for RNA viruses
- A61P31/18—Antivirals for RNA viruses for HIV
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/20—Preparation of carboxylic acid nitriles by dehydration of carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Virology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- AIDS & HIV (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP02078306 | 2002-08-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT1529032E true PT1529032E (pt) | 2013-07-11 |
Family
ID=31725448
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT37878139T PT1529032E (pt) | 2002-08-09 | 2003-08-07 | Processos para a preparação de 4-[[(4-[[4-(2-cianoetenilo)-2,6 dimetilofenilo]amino]-2-pirimidinilo]amino]benzonitrilo |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US7399856B2 (de) |
| EP (1) | EP1529032B1 (de) |
| JP (1) | JP4822707B2 (de) |
| KR (2) | KR101086678B1 (de) |
| CN (4) | CN102702111B (de) |
| AR (1) | AR040964A1 (de) |
| AU (1) | AU2003266413B2 (de) |
| CA (2) | CA2493794C (de) |
| CL (1) | CL2010000284A1 (de) |
| CY (1) | CY1114428T1 (de) |
| DK (1) | DK1529032T3 (de) |
| EA (1) | EA007953B1 (de) |
| ES (1) | ES2422196T3 (de) |
| HR (1) | HRP20050104B1 (de) |
| IL (1) | IL166710A (de) |
| IS (1) | IS2980B (de) |
| MX (1) | MXPA05001541A (de) |
| MY (1) | MY144894A (de) |
| NO (1) | NO330013B1 (de) |
| NZ (1) | NZ538611A (de) |
| PL (1) | PL208533B1 (de) |
| PT (1) | PT1529032E (de) |
| SI (1) | SI1529032T1 (de) |
| TW (1) | TWI314146B (de) |
| WO (1) | WO2004016581A1 (de) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7638522B2 (en) * | 2001-08-13 | 2009-12-29 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino] benzonitrile |
| JO3429B1 (ar) | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| MY169670A (en) | 2003-09-03 | 2019-05-08 | Tibotec Pharm Ltd | Combinations of a pyrimidine containing nnrti with rt inhibitors |
| US8101629B2 (en) * | 2001-08-13 | 2012-01-24 | Janssen Pharmaceutica N.V. | Salt of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile |
| CN102702111B (zh) * | 2002-08-09 | 2014-12-17 | 詹森药业有限公司 | 制备4-[[4-[[4-(2-氰基乙烯基)-2,6-二甲基苯基]氨基]-2-嘧啶基]氨基]苄腈的方法 |
| KR20050084027A (ko) * | 2002-11-28 | 2005-08-26 | 쉐링 악티엔게젤샤프트 | Ｃｈｋ-, ｐｄｋ- 및 ａｋｔ-억제성 피리미딘, 그의제조방법 및 약제로서의 그의 용도 |
| WO2005123662A1 (en) * | 2004-06-18 | 2005-12-29 | Janssen Pharmaceutica N.V. | Modified heck reaction |
| WO2006024668A1 (en) * | 2004-09-02 | 2006-03-09 | Janssen Pharmaceutica N.V. | Hydrochloride of 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl] amino]benzonitrile |
| MX2007002594A (es) * | 2004-09-02 | 2007-04-25 | Janssen Pharmaceutica Nv | Fumarato de 4-((4-((4- (2-cianoetenil)-2, 6-dimetilfenil) amino)-2-pirimidinil) amino) benzonitrilo. |
| DK1632232T6 (da) * | 2004-09-02 | 2022-04-19 | Janssen Pharmaceutica Nv | Salt af 4-[[4-[[4-(2-cyanoethenyl)-2,6-dimethylphenyl]amino]-2-pyrimidinyl]¬amino]¬benzonitril |
| UA92467C2 (ru) * | 2004-09-02 | 2010-11-10 | Янссен Фармацевтика Н.В. | Гидрохлорид 4-[[4-[[4-(2-цианоэтенил)-2,6-диметилфенил]амино]-2-пиримидинил]амино]бензонитрила |
| WO2006024667A1 (en) * | 2004-09-02 | 2006-03-09 | Janssen Pharmaceutica N.V. | Furamate of 4-( (4-( (4- (2-cyanoethenyl) -2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)benzonitrile |
| US7314962B2 (en) * | 2005-04-15 | 2008-01-01 | E. I. Du Pont De Nemours & Co. | Alkylation of aromatic compounds |
| ES2437202T3 (es) * | 2005-05-26 | 2014-01-09 | Janssen R&D Ireland | Procedimiento para preparar 4-[(1,6-dihidro-6-oxo-2-pirimidinil)-amino]benzonitrilo |
| AR065720A1 (es) | 2007-03-14 | 2009-06-24 | Tibotec Pharm Ltd | Polvos para reconstitucion que comprenden rilpivirina dispersos en ciertos polimeros. uso. proceso. |
| US8426434B2 (en) * | 2007-07-12 | 2013-04-23 | Tibotec Pharmaceuticals Ltd. | Crystalline form of 4-[[4-[[4-(2-Cyanoethenyl)-2,6-dimethylphenyl]-amino]-2-pyrimidinyl]amino]benzonitrile |
| WO2012125993A1 (en) | 2011-03-17 | 2012-09-20 | Teva Pharmaceutical Industries Ltd. | Solid state forms of rilpivirine base, and rilipivirine salts |
| EP2643294B1 (de) * | 2011-04-15 | 2016-08-24 | Emcure Pharmaceuticals Limited | Verbessertes rilpivirinverfahren |
| EP2702044B1 (de) | 2011-04-25 | 2017-03-22 | Hetero Research Foundation | Verfahren für rilpivirin |
| EP2755959B1 (de) * | 2011-09-16 | 2018-05-16 | Hetero Research Foundation | Rilpivirin-hydrochlorid |
| WO2013170421A1 (zh) * | 2012-05-14 | 2013-11-21 | 上海迪赛诺药业有限公司 | 利匹韦林盐酸盐醇化物多晶型物及其制备方法 |
| WO2013179105A1 (en) * | 2012-06-01 | 2013-12-05 | Laurus Labs Private Limited | Improved process for preparation of rilpivirine and pharmaceutically acceptable salts thereof |
| WO2014009968A2 (en) * | 2012-07-12 | 2014-01-16 | Hetero Research Foundation | Process for rilpivirine using novel intermediate |
| CZ201532A3 (cs) | 2015-01-21 | 2015-02-25 | Zentiva, K.S. | Způsob výroby vysoce čistého Rilpivirinu a jeho solí |
| CN106008366A (zh) * | 2016-05-25 | 2016-10-12 | 山东大学 | 一种利匹韦林的制备方法 |
| RS65159B1 (sr) | 2016-10-24 | 2024-02-29 | Janssen Sciences Ireland Unlimited Co | Disperzibilni sastavi |
| US20210380540A1 (en) | 2018-10-25 | 2021-12-09 | Minakem | Process for the preparation of rilpivirine |
| CN110526873B (zh) * | 2019-08-15 | 2022-09-16 | 复旦大学 | 氰乙烯基取代的苯并二芳基嘧啶类化合物及其制备方法和用途 |
| US11166952B2 (en) | 2019-11-29 | 2021-11-09 | Aptorum Therapeutics Limited | Composition including rilpivirine and method for treating tumors or cancer |
| CN112010810B (zh) * | 2020-09-09 | 2024-01-30 | 瑞阳制药股份有限公司 | 一锅法制备高纯度利匹韦林中间体的方法 |
| CN112778214A (zh) * | 2021-01-13 | 2021-05-11 | 安徽贝克联合制药有限公司 | 用于合成利匹韦林的中间体、其合成方法和利匹韦林的合成方法 |
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| US3459731A (en) * | 1966-12-16 | 1969-08-05 | Corn Products Co | Cyclodextrin polyethers and their production |
| EP0002341B1 (de) | 1977-11-28 | 1982-01-20 | Barry Boettcher | Zweiwertige Kupferkomplexe, Verfahren zu deren Herstellung und solche Komplexe enthaltende Zusammensetzungen |
| US5691364A (en) * | 1995-03-10 | 1997-11-25 | Berlex Laboratories, Inc. | Benzamidine derivatives and their use as anti-coagulants |
| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| HUP9900730A3 (en) | 1995-11-23 | 2001-04-28 | Janssen Pharmaceutica Nv | Solid mixtures of cyclodextrins prepared via melt-extrusion |
| GB9705361D0 (en) | 1997-03-14 | 1997-04-30 | Celltech Therapeutics Ltd | Chemical compounds |
| US6982091B2 (en) * | 2001-08-29 | 2006-01-03 | Umd, Inc. | Vaginal delivery of chemotherapeutic agents and inhibitors of membrane efflux systems for cancer therapy |
| ES2361146T3 (es) * | 1998-03-27 | 2011-06-14 | Janssen Pharmaceutica Nv | Derivados de la piramidina inhibitatoria de vih. |
| AU751573C (en) * | 1998-03-27 | 2003-10-09 | Janssen Pharmaceutica N.V. | HIV inhibiting pyrimidine derivatives |
| JP2000035628A (ja) | 1998-07-16 | 2000-02-02 | Konica Corp | ハロゲン化銀写真感光材料 |
| DE69933680T2 (de) | 1998-08-29 | 2007-08-23 | Astrazeneca Ab | Pyrimidine verbindungen |
| JP3635238B2 (ja) * | 1998-11-10 | 2005-04-06 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | Ｈｉｖの複製を阻害するピリミジン類 |
| AU759875B2 (en) | 1999-03-09 | 2003-05-01 | Pharmacia & Upjohn Company | 4-OXO-4,7-dihydro-thieno(2,3-b)pyridine-5-carboxamides as antiviral agents |
| NZ513639A (en) | 1999-04-15 | 2004-02-27 | Bristol Myers Squibb Co | Cyclic protein tyrosine kinase inhibitors |
| GB9914258D0 (en) | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| DE60025837T2 (de) | 1999-09-24 | 2006-11-02 | Janssen Pharmaceutica N.V. | Antivirale feste dispersionen |
| DE19945982A1 (de) * | 1999-09-24 | 2001-03-29 | Knoll Ag | Geschwindigkeitsbestimmte Partikel |
| HUP0301117A3 (en) | 2000-02-17 | 2004-01-28 | Amgen Inc Thousand Oaks | Imidazole derivatives kinase inhibitors, their use, process for their preparation and pharmaceutical compositions containing them |
| GB0004887D0 (en) * | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| GB0004888D0 (en) | 2000-03-01 | 2000-04-19 | Astrazeneca Uk Ltd | Chemical compounds |
| US7276510B2 (en) * | 2000-05-08 | 2007-10-02 | Janssen Pharmaceutica, Inc. | HIV replication inhibitors |
| US6596729B2 (en) * | 2000-07-20 | 2003-07-22 | Bristol-Myers Squibb Company | Tricyclic-2-pyridone compounds useful as HIV reverse transcriptase inhibitors |
| CN1494528A (zh) | 2001-03-02 | 2004-05-05 | ʷ��˿�������ȳ�ķ����˾ | 作为逆转录酶抑制剂的二苯酮 |
| ES2292753T4 (es) * | 2001-03-29 | 2009-02-16 | Vertex Pharmaceuticals Incorporated | Inhibidores de quinasas n-terminales c-jun (jnk) y otras proteina quinasas. |
| JO3429B1 (ar) * | 2001-08-13 | 2019-10-20 | Janssen Pharmaceutica Nv | مشتقات برميدينات مثبطة فيروس الايدز |
| MY169670A (en) | 2003-09-03 | 2019-05-08 | Tibotec Pharm Ltd | Combinations of a pyrimidine containing nnrti with rt inhibitors |
| TWI329105B (en) * | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| PL220850B1 (pl) * | 2002-05-03 | 2016-01-29 | Janssen Pharmaceutica Nv | Kopolimer dwublokowy, kompozycja zawierająca składnik aktywny i jej zastosowanie oraz sposób jej wytwarzania |
| CN102702111B (zh) * | 2002-08-09 | 2014-12-17 | 詹森药业有限公司 | 制备4-[[4-[[4-(2-氰基乙烯基)-2,6-二甲基苯基]氨基]-2-嘧啶基]氨基]苄腈的方法 |
| AU2002350719A1 (en) | 2002-11-29 | 2004-06-23 | Janssen Pharmaceutica N.V. | Pharmaceutical compositions comprising a basic respectively acidic drug compound, a surfactant and a physiologically tolerable water-soluble acid respectively base |
-
2003
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- 2003-08-07 KR KR1020107026275A patent/KR101086678B1/ko not_active Expired - Lifetime
- 2003-08-07 NZ NZ538611A patent/NZ538611A/en not_active IP Right Cessation
- 2003-08-07 US US10/523,753 patent/US7399856B2/en not_active Expired - Lifetime
- 2003-08-07 CA CA2493794A patent/CA2493794C/en not_active Expired - Lifetime
- 2003-08-07 PL PL373679A patent/PL208533B1/pl unknown
- 2003-08-07 CN CN200910001327XA patent/CN101481356B/zh not_active Expired - Lifetime
- 2003-08-07 HR HRP20050104AA patent/HRP20050104B1/hr not_active IP Right Cessation
- 2003-08-07 MY MYPI20032999A patent/MY144894A/en unknown
- 2003-08-07 CN CNB038192764A patent/CN100554245C/zh not_active Expired - Lifetime
- 2003-08-07 KR KR1020057000881A patent/KR101140785B1/ko not_active Expired - Lifetime
- 2003-08-07 PT PT37878139T patent/PT1529032E/pt unknown
- 2003-08-07 CA CA2686429A patent/CA2686429C/en not_active Expired - Lifetime
- 2003-08-07 DK DK03787813.9T patent/DK1529032T3/da active
- 2003-08-07 SI SI200332275T patent/SI1529032T1/sl unknown
- 2003-08-07 JP JP2004528518A patent/JP4822707B2/ja not_active Expired - Lifetime
- 2003-08-07 EP EP03787813.9A patent/EP1529032B1/de not_active Expired - Lifetime
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- 2003-08-07 CN CN2011101114129A patent/CN102225902B/zh not_active Expired - Lifetime
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- 2003-08-07 EA EA200500325A patent/EA007953B1/ru unknown
- 2003-08-07 MX MXPA05001541A patent/MXPA05001541A/es active IP Right Grant
- 2003-08-07 WO PCT/EP2003/050366 patent/WO2004016581A1/en not_active Ceased
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- 2003-08-08 AR ARP030102882A patent/AR040964A1/es active IP Right Grant
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2004
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2008
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2010
- 2010-03-29 CL CL2010000284A patent/CL2010000284A1/es unknown
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2013
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